


Pretty

by TheWincestRiots



Category: Supernatural
Genre: Feminization, M/M
Language: English
Status: Completed
Published: 2015-05-25
Updated: 2015-05-25
Packaged: 2018-04-01 02:57:58
Rating: Not Rated
Warnings: Underage
Chapters: 1
Words: 968
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/4003237
Author URL: https://archiveofourown.org/users/TheWincestRiots/pseuds/TheWincestRiots





	Pretty

This was a side of Dean that only Sam ever got to see, and it was beautiful.

He sometimes wondered what it would be like if Dean could be like this all the time, but he couldn’t, of course. He was Dean Winchester, John Winchester’s son, hunter extraordinaire, and he had a reputation to uphold. Sam didn’t think it was very fair, but the world they live in would never be accepting of this.

Sam was fifteen when he found out, already completely wrapped up in his feelings for his older brother and so intent on hiding them that he never noticed Dean was keeping secrets of his own.

He was supposed to be at school, but he wasn’t feeling well so he’d left after lunch, he’d only be missing study hall and gym anyway. He’d quietly let himself into the cottage they were squatting in, noiselessly putting down his backpack and toeing off his shoes. He’d gotten very good at being quiet, didn’t like to make too much noise or take up too much space or call attention to himself in any way. He wasn’t expecting anyone to be home, Dad was off on a hunt and Dean was usually out when Sam came home from school. He made his way to the tiny bedroom he and Dean shared, thinking of nothing more than curling on his bed and going to sleep. When he looked through the open door all thoughts of sleep fled instantly from his mind.

Dean stood in front of the mirrored closet door wearing rosy pink panties and an old white t-shirt, too small and thin with wear, the neck cut off to expose his collarbones. Dean was turned away from him but Sam could see in the mirror that he was applying lip gloss, the kind with a little wand set into the cap like the girls at school used. He was completely unaware of his body at that moment (completely unaware of anything other than his brother) but he must have made some sort of noise because Dean suddenly turned to the door, dropping the tube of gloss with a plasticky clatter on the hard wood floor.

“S-Sam…I-” Despite the look of blind panic on his face, all Sam could think was how beautiful he looked. Sam always thought Dean was beautiful, but now…The shimmery pink shine on his full lips, the smudge of eyeliner making his green eyes look even bigger and greener, the faint stain of pink blush accentuating his cheekbones, it took Sam’s breath away.

“Sammy, please, you can’t tell anyone. Please don’t tell Dad, Sam.” His voice had a desperate pleading note to it, an undercurrent of fear, and Sam could hear what Dean wasn’t saying - _please don’t hate me_.

Sam crossed the room to where Dean was standing, looking like he was steeling himself for a punch. He tentatively reached out his arm toward Dean, gently laying his palm on Dean’s cheek.

“I’ll always keep your secrets Dean” His relief was so palpable Sam could feel it through his hand as Dean relaxed, leaning slightly into Sam’s touch. It would be so easy to pull him close and kiss him, and Sam wanted that right now more than he’d ever wanted anything. He let his hand fall and stepped back, giving himself a slight shake.

“I uh… I left school early ‘cause I don’t feel too good. I’m just gonna lie down for a while.” Sam gestured towards the bed. “But, we can still talk, I mean, if you want to.”

Dean nodded. “I’ll shut the blinds for you.”

Sam curled up on his side on the messy unmade bed, not bothering to pull up the covers. He felt the bed dip behind him as Dean settled, leaning against the headboard. When he spoke his voice was as quiet as Sam had ever heard it.

“It’s not like I want to be a girl. I like having a cock, and I like fucking girls.”

Sam closed his eyes. _I know,_ he thought.

"I just like to…look pretty. I like the way it makes me feel. And…it… it makes me look like Mom, makes me feel a little closer to her. I don’t know. Sam… I think…I think I might like guys, too. Or, well, one guy, anyway.“

Sam let that sink in for a moment before slowly rolling over to face his brother. He was curious, but he felt that now wasn’t really the time to ask questions, right now Dean needed reassurance and acceptance.

"Dean” Sam reached out and let his hand rest on Dean’s forearm. “I think you look beautiful.”

Dean’s mouth turned up in a small smile, a pale ghost of his regular cocky grin, the tips of his ears turning pink as a blush spread cross his face.

“Yeah?”

Sam smiled up at him, full and bright, his fingers trailing lightly over Dean’s arm. “Yeah.”

Dean shifted down so that he was nose to nose with Sam and Sam thought he was even prettier close up. He felt like his chest was about to burst open and release a swarm of butterflies.

He felt Dean’s breath warm on his face as he whispered “Sam…”

And he couldn’t stand it anymore, could’t stop himself. He inched forward and kissed Dean. It was soft and sweet and chaste and instead of pulling back like Sam expected, Dean kissed him back, threading his fingers into the hair at the nape of Sam’s neck. Sam stroked down Dean’s back and giggled softly as he rested his forehead against his brother’s.

“What’s so funny?” Dean asked.

“It’s peach.” He said, bringing his fingers up to Dean’s lips, “I was sure it would be cherry.”

Dean laughed, pulling Sam in for another taste.


End file.
